Dean Winchester & the Burden of Pretty
This is how I see the young Dean Winchester. Way prettier than Brock Kelly. (Although I think this argument works even if we go with canon Brock.) He wasn’t 6’1” yet. He didn’t have those broad shoulders. He might have been strong for his size, but it didn’t show. He might have had callouses on his hands from handling weapons, but his cheeks were smooth and soft.
Imagine this kid in a room full of hunters — trying to prove to them and to his dad that he’s tough, he’s competent. Imagine him as the new kid in school, again and again, year after year. Sure the girls are all swoony, but the boys … imagine the taunts, the implied threats, the shoves and punches before he learned to strike back.
It wasn’t just monsters that made Dean tough. It was his own pretty face, and he hated it. It wasn’t until later that he learned to use it to his advantage. It became a kind of weapon too. Still, he knows, it’s a double edged sword — as much a weakness as a strength.
Poor kid. Can you imagine looking like this and being John Winchester’s son? Being a hunter? Being the new kid in school all the time? No wonder he puts up that macho front and hits on all the girls. He’s got something to prove — that those things the other boys say about his mouth aren’t true, that he can kill monsters better than most hunters, that he isn’t weak or girly or gay. And I have no doubt that John was tougher on him because of the way he looked. He thought, in that warped ex-Marine way of his, that he needed to be. That being tougher on him would make Dean tougher, but it didn’t. It made him more insecure and more defensive. You don’t see Sam overcompensating the way Dean does, and I think that’s the root of it. Sam was a cute; Dean was pretty. He’s still pretty like the vamp said. Dean pretends he hasn’t heard it a thousand times before, but he has. And it still makes his stomach twist with the memories of propositions that sounded like threats from strange men in rest areas and bars and motel walkways. If Dean has an attraction for men, he’s very ambivalent about it. If he’s acted on it, he’d have to be in control. He’d never allow himself to be vulnerable with another man. (Well, maybe one 😉
Dean always had to overcompensate with the whole badass, macho, man whore schtick when he was young because it was hard being a hunter when he was so damn pretty. His dad’s hunter friends never took him seriously. He got hit on by men at the bars and motels they frequented when he was a kid. The way some of the other guys looked at him every time he was the new kid in school made him kind of uncomfortable. It didn’t help that he kind of liked it. He taught the others quickly that he couldn’t be bullied, but it was still one of the reasons he quit going to school.
Even though Sammy wasn’t as pretty, Dean’s experiences made him more protective of his little brother — almost possessive. He didn’t want Sam experiencing that weird twisty feeling in his gut, that implied threat in another man’s eyes, not of violence — not a fist in the gut violence, but something else — a theft of control, a violation. He never let it happen to him or Sammy. It’s one thing he’s proud of in his life.